Cimicifugic acid B

Details

• Internal ID: 3c176ae3-6deb-44ba-848d-496b8dfa2638
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxybutanedioic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC(=O)OC(C(=O)O)C(CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C(=O)O[C@H](C(=O)O)[C@](CC2=CC(=C(C=C2)O)O)(C(=O)O)O)O
• InChI: InChI=1S/C21H20O11/c1-31-16-6-3-11(8-15(16)24)4-7-17(25)32-18(19(26)27)21(30,20(28)29)10-12-2-5-13(22)14(23)9-12/h2-9,18,22-24,30H,10H2,1H3,(H,26,27)(H,28,29)/b7-4+/t18-,21-/m1/s1
• InChI Key: YVHLLZXSGPDXOA-ZHBFVYIWSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 1.50

Synonyms

• 205114-66-5
• RMQ0SKL6CI
• UNII-RMQ0SKL6CI
• CIMICIFUGA ACID B
• (2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxybutanedioic acid
• Butanedioic acid, 2-9(3,4-dihydroxyphenyl)methyl)-2-hydroxy-3-(((2E)-3-(3-hydroxy-4-methoxyphenyl)-1-oxo-2-propenyl)oxy)-, (2R,3S)-
• Butanedioic acid, 2-9(3,4-dihydroxyphenyl)methyl)-2-hydroxy-3-((3-(3-hydroxy-4-methoxyphenyl)-1-oxo-2-propenyl)oxy)-, (S-(R*,S*(E)))-
• BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-(((2E)-3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (2R,3S)-
• BUTANEDIOIC ACID, 2-((3,4-DIHYDROXYPHENYL)METHYL)-2-HYDROXY-3-((3-(3-HYDROXY-4-METHOXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (S-(R*,S*-(E)))-
• CHEMBL500586
• DTXSID801347722
• AKOS040761499
• Q27288197
• NCGC00380872-01!(2R,3S)-2-[(3,4-dihydroxyphenyl)methyl]-2-hydroxy-3-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxybutanedioic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.11%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.10%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.19%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.96%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	94.99%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.91%	96.00%
CHEMBL1255126	O15151	Protein Mdm4	94.35%	90.20%
CHEMBL2581	P07339	Cathepsin D	94.15%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	93.88%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.66%	95.56%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	91.47%	80.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.74%	94.45%
CHEMBL3194	P02766	Transthyretin	88.96%	90.71%
CHEMBL2535	P11166	Glucose transporter	87.82%	98.75%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	82.94%	92.29%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.77%	90.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.10%	96.09%

Plants that contains it

• Actaea cimicifuga
• Actaea dahurica
• Actaea heracleifolia
• Actaea racemosa
• Actaea simplex

Cross-Links

• PubChem: 6449880
• NPASS: NPC221383
• ChEMBL: CHEMBL500586
• LOTUS: LTS0172777
• wikiData: Q27288197